CA1289476C - Ionic heparin coating - Google Patents
Ionic heparin coatingInfo
- Publication number
- CA1289476C CA1289476C CA000521942A CA521942A CA1289476C CA 1289476 C CA1289476 C CA 1289476C CA 000521942 A CA000521942 A CA 000521942A CA 521942 A CA521942 A CA 521942A CA 1289476 C CA1289476 C CA 1289476C
- Authority
- CA
- Canada
- Prior art keywords
- heparin
- complex
- medical article
- coating
- article
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229960002897 heparin Drugs 0.000 title claims abstract description 63
- 229920000669 heparin Polymers 0.000 title claims abstract description 63
- 238000000576 coating method Methods 0.000 title claims abstract description 34
- 239000011248 coating agent Substances 0.000 title claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000002091 cationic group Chemical group 0.000 claims abstract description 9
- 230000001453 nonthrombogenic effect Effects 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 8
- 239000008280 blood Substances 0.000 claims description 22
- 210000004369 blood Anatomy 0.000 claims description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 20
- 239000011780 sodium chloride Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- -1 cationic alkylbenzyl dimethyl ammonium salt Chemical class 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- 239000002952 polymeric resin Substances 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
- 229920003002 synthetic resin Polymers 0.000 claims description 5
- 230000002965 anti-thrombogenic effect Effects 0.000 claims description 4
- 238000009877 rendering Methods 0.000 claims description 4
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical group CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 3
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 18
- 238000012360 testing method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 102000008946 Fibrinogen Human genes 0.000 description 9
- 108010049003 Fibrinogen Proteins 0.000 description 9
- 229940012952 fibrinogen Drugs 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 238000003795 desorption Methods 0.000 description 6
- 238000002386 leaching Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229960000686 benzalkonium chloride Drugs 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000007536 Thrombosis Diseases 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 239000002473 artificial blood Substances 0.000 description 2
- 229960001716 benzalkonium Drugs 0.000 description 2
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940127090 anticoagulant agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
- A61L33/0017—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using a surface active agent
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US820,670 | 1977-08-01 | ||
| US82067086A | 1986-01-21 | 1986-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1289476C true CA1289476C (en) | 1991-09-24 |
Family
ID=25231433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000521942A Expired - Lifetime CA1289476C (en) | 1986-01-21 | 1986-10-31 | Ionic heparin coating |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0231573B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS62172961A (enrdf_load_stackoverflow) |
| CA (1) | CA1289476C (enrdf_load_stackoverflow) |
| DE (1) | DE3682389D1 (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2028069C (en) * | 1989-11-02 | 2001-02-20 | Richard James Whitbourne | Anti-thrombogenic, and/or anti-microbial composition |
| US5525348A (en) * | 1989-11-02 | 1996-06-11 | Sts Biopolymers, Inc. | Coating compositions comprising pharmaceutical agents |
| KR940006893B1 (ko) * | 1990-02-26 | 1994-07-28 | 삼성전자 주식회사 | 비데오 테이프의 프레임 탐색방법 |
| EP0588895B1 (en) * | 1991-05-31 | 1995-01-11 | Baxter International Inc. | Thromboresistant coating for defoaming applications |
| EP0769503A3 (en) * | 1995-10-17 | 1997-10-08 | Terumo Corp | Heparin complex and medical device containing such compound |
| JP4505871B2 (ja) * | 1999-04-07 | 2010-07-21 | 株式会社ジェイ・エム・エス | 抗血栓性ムコ多糖処理した血流接触医療用部材、および該血流接触医療用部材の製造法 |
| JP4703954B2 (ja) * | 2003-09-04 | 2011-06-15 | 財団法人浜松科学技術研究振興会 | 基材の親水化処理方法および親水性基材 |
| JP4046146B1 (ja) | 2007-04-23 | 2008-02-13 | 東洋紡績株式会社 | 中空糸膜型人工肺および処理方法 |
| JP5152212B2 (ja) * | 2010-01-30 | 2013-02-27 | 株式会社ジェイ・エム・エス | 血流接触医療用部材、および該血流接触医療用部材の製造法 |
| WO2017134049A1 (en) | 2016-02-01 | 2017-08-10 | Schierholz Jörg Michael | Implantable medical products, a process for the preparation thereof, and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE400173B (sv) * | 1975-03-20 | 1978-03-20 | Aminkemi Ab | Forfarande vid stabilisering av en hepariniserad yta innehallande vid blodkontakt utlosbart heparin |
-
1986
- 1986-07-03 DE DE8686305172T patent/DE3682389D1/de not_active Expired - Lifetime
- 1986-07-03 EP EP19860305172 patent/EP0231573B1/en not_active Expired
- 1986-10-31 CA CA000521942A patent/CA1289476C/en not_active Expired - Lifetime
- 1986-12-01 JP JP61284458A patent/JPS62172961A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0231573A2 (en) | 1987-08-12 |
| EP0231573B1 (en) | 1991-11-06 |
| DE3682389D1 (de) | 1991-12-12 |
| EP0231573A3 (en) | 1989-07-26 |
| JPS62172961A (ja) | 1987-07-29 |
| JPH0236267B2 (enrdf_load_stackoverflow) | 1990-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |